17-氧代十八酸 | 16694-38-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 17-氧代十八酸
• 英文名称: 17-oxo-octadecanoic acid
• 英文别名: 17-Oxo-octadecansaeure；17-Oxo-octadecansaeure-(1)；17-Oxo-stearinsaeure；17-oxooctadecanoic acid
• CAS: 16694-38-5
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: WMMNNWMMXHQOPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-氧代十八酸 生成 甲基17-氧代硬脂酸酯
  参考文献：
  名称：

  HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE

  摘要：

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。

  DOI：

  10.1139/v61-104
• 作为产物：
  描述：

  甲基15-溴十五烷酸酯 在 potassium carbonate 、 2-戊酮 、 丙酮 、 sodium iodide 作用下， 生成 17-氧代十八酸
  参考文献：
  名称：

  Bergstroem et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 1157,1160, 1169

  摘要：

  DOI：

文献信息

• Solid phase method for synthesis peptide-spacer-lipid conjugates, conjugates synthesized thereby and targeted liposomes containing the same
  申请人：DEVELOPMENT CENTER FOR BIOTECHNOLOGY

  公开号：US20030229017A1

  公开（公告）日：2003-12-11

  A solid phase synthesis method for preparing peptide-spacer-lipid conjugates, the peptide-spacer-lipid conjugates synthesized by the method, and liposomes containing the peptide-spacer-lipid conjugates. The present invention provides a convenient solid phase synthesis method for preparing peptide-spacer-lipid conjugates and provides various linkage groups (such as amide group) for conjugating peptide, spacer and lipid, wherein the spacer may comprise PEG. Several advantages can be achieved, such as the synthetic procedure can be simplified, the synthesis process can be set to automation, the purification is easier in each reaction step, and the product losses can be reduced to minimal during synthesis. The present synthesis method is suitable for preparing a wide range of peptide-spacer-lipid conjugates, provides a peptide-spacer-lipid conjugate prepared by the solid phase synthesis method of the present invention, which can be incorporated into a liposome as the targeting moiety for liposomal drug delivery to specific cells, and provides a targeting liposome containing the present peptide-spacer-lipid conjugate.

  一种用于制备肽-间隔子-脂质共轭物的固相合成方法，所述方法合成的肽-间隔子-脂质共轭物，以及含有肽-间隔子-脂质共轭物的脂质体。本发明提供了一种便利的固相合成方法，用于制备肽-间隔子-脂质共轭物，并提供了各种连接基团（如酰胺基团）用于连接肽、间隔子和脂质，其中间隔子可以包括PEG。可以实现几项优点，例如合成过程可以简化，合成过程可以设定为自动化，每个反应步骤中的纯化更容易，并且在合成过程中产品损失可以降至最低。本合成方法适用于制备各种肽-间隔子-脂质共轭物，提供了一种由本发明的固相合成方法制备的肽-间隔子-脂质共轭物，可作为靶向单元被纳入脂质体，用于将脂质体药物传递到特定细胞，并提供了含有本肽-间隔子-脂质共轭物的靶向脂质体。
• Microbiological oxidation of long-chain aliphatic compounds. Part I. Alkanes and alk-1-enes
  作者：D. F. Jones、R. Howe

  DOI：10.1039/j39680002801

  日期：——

  to the corresponding alkanoic acids. These acids are metabolised, either by β-oxidation, or by hydroxylation to give ω-hydroxy-acids (and subsequently αω-dicarboxylic acids) and, by a stereospecific hydroxylation, ω-1-hydroxy-acids. The oxidised alkanoic acids are protected from further degradation by incorporation into glycolipids. The chain-length of an alkanoic acid determines (i) whether β-oxidation

  酵母Torulopsis gropengiesseri将长链烷烃转化为糖脂，其中糖脂掺入了烷烃的氧化衍生物。源自C 12 -C 24的糖脂脂质成分的比较烷烃，各种氧化的烷烃衍生物以及一系列的β-烷氧基丙酸甲酯表明，烷烃代谢的主要途径涉及烷烃1-醇的形成，随后将其脱氢为相应的链烷酸。这些酸通过β-氧化或通过羟基化代谢以生成ω-羟基酸（随后是αω-二羧酸），并通过立体有择羟基化代谢成ω-1-羟基酸。通过结合到糖脂中，可以保护氧化的链烷酸免于进一步降解。链烷酸的链长决定（i）β-氧化或羟基化是主要反应，以及（ii）羟基化主要发生在ω-或ω-1-位。当羟基化位点和羧基被14个亚甲基链隔开时，链烷酸的ω-和ω-1-羟基化效率最高。提出这些羟基化可以通过单一酶来实现。烷烃代谢的次要途径涉及形成烷烃-2-醇，其被掺入糖脂中而不被氧化代谢。长链烷-1-烯的发酵产生糖脂，其掺入衍生自烷-1-烯的ω-1-羟基
• THE FERMENTATION OF LONG-CHAIN COMPOUNDS BY TORULOPSIS MAGNOLIAE: I. STRUCTURES OF THE HYDROXY FATTY ACIDS OBTAINED BY THE FERMENTATION OF FATTY ACIDS AND HYDROCARBONS
  作者：A. P. Tulloch、J. F. T. Spencer、P. A. J. Gorin

  DOI：10.1139/v62-203

  日期：1962.7.1

  The yield of extracellular glycolipid produced by Torulopsis magnoliae is increased three-to five-fold by the addition of suitable compounds to the growing culture. The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydroxylated and converted to hydroxy fatty acid sophorosides. Fatty esters of all chain lengths from C₁₆to C₂₂, including several unsaturated esters, and even-numbered hydrocarbons from C₁₆to C₂₄are readily fermented. Shorter-chain compounds are used poorly or not at all. With compounds of 16 to 18 carbon atoms, hydroxylation occurs at the terminal or penultimate carbon atom, depending on degree of unsaturation and chain length. Substrates of more than 18 carbon atoms are mainly reduced in chain length by one or more two-carbon units and hydroxylated, giving C₁₇or C₁₈acids with the hydroxyl group on the penultimate carbon atom. The various enzymic reactions which occur during the fermentation are discussed.

  扩大培养基中添加适当化合物可将Magnoliae酵母产生的细胞外糖脂产量提高三到五倍。这种添加剂可以是长链酸、酯、碳氢化合物或甘油酯，经过羟基化后转化为羟基脂肪酸索非酮苷。从C16到C22的所有链长的脂肪酯，包括几种不饱和酯，以及从C16到C24的偶数碳氢化合物都容易发酵。较短链的化合物使用效果不佳或根本不使用。对于含有16到18个碳原子的化合物，羟基化发生在末端或次末端碳原子上，取决于不饱和度和链长。含有超过18个碳原子的底物主要通过一个或多个二碳单位减少链长并进行羟基化，从而在次末端碳原子上带有羟基的C17或C18酸。讨论了发酵过程中发生的各种酶反应。
• Novel macrocyclic glycolipids from Torulopsis gropengiesseri
  作者：D. F. Jones

  DOI：10.1039/j39670000479

  日期：——

  Chemical and spectroscopic evidence is presented in support of a proposed structure for the crystalline glycolipid which is formed during fermentation of Torulopsis gropengiesseri in a medium supplemented by methyl 9-octa-decenoate. Closely related macrocyclic lactones are formed by fermentations in media supplemented by n-heptadecane, n-hexadecane, and methyl hexadecanoate and also in a medium lacking

  提出了化学和光谱学证据以支持拟议的糖脂晶体的拟议结构，该糖脂结构是在由拟南芥（Torulopsis gropengiesseri）在补充有9-辛烯-癸烯酸甲酯的培养基中发酵期间形成的。紧密相关的大环内酯是通过在正庚烷，正十六烷和十六烷酸甲酯补充的培养基中以及缺乏补充剂的培养基中发酵形成的。
• [EN] RELEASABLE CATIONIC LIPIDS FOR NUCLEIC ACIDS DELIVERY SYSTEMS<br/>[FR] LIPIDES CATIONIQUES LIBÉRABLES POUR SYSTÈMES D'ADMINISTRATION D'ACIDES NUCLÉIQUES
  申请人：ENZON PHARMACEUTICALS INC

  公开号：WO2010057155A1

  公开（公告）日：2010-05-20

  The present invention is directed to releasable cationic lipids and nanoparticle compositions for the delivery of nucleic acids and methods of modulating an expression of a target gene using the same. In particular, the invention relates to cationic lipids including an acid labile linker, and nanoparticle compositions containing the same.

  本发明涉及可释放的阳离子脂质和纳米颗粒组合物，用于传递核酸并利用其调节靶基因的表达的方法。具体而言，本发明涉及包含酸敏感连接剂的阳离子脂质和含有该连接剂的纳米颗粒组合物。